Artifact-free matrix-assisted laser desorption ionization time-of-flight mass spectra of tert.-butyldimethylsilyl ether derivatives of cyclodextrins used for the synthesis of single-isomer, chiral resolving agents for capillary electrophoresis

Russell, William K.; Russell, David H.; Busby, M. Brent; Kolberg, A.; Li, S.; Maynard, Dawn Kirby; Sanchez-Vindas, Silvia; Zhu, Wenhong; Vigh, Gy.

doi:10.1016/s0021-9673(00)01264-4

Cited by 16 publications

(7 citation statements)

References 64 publications

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“…However, the nonacidic matrix, THAP has enabled the derivatives to be examined intact with negligible loss of TBDMS groups (Russell et al, 2001). …”

Section: Cyclodextrins and Related Compoundsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Harvey¹

2008

Mass Spectrometry Reviews

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This review is the second update of the original review on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates that was published in 1999. It covers fundamental aspects of the technique as applied to carbohydrates, fragmentation of carbohydrates, studies of specific carbohydrate types such as those from plant cell walls and those attached to proteins and lipids, studies of glycosyl-transferases and glycosidases, and studies where MALDI has been used to monitor products of chemical synthesis. Use of the technique shows a steady annual increase at the expense of older techniques such as FAB. There is an increasing emphasis on its use for examination of biological systems rather than on studies of fundamental aspects and method development and this is reflected by much of the work on applications appearing in tabular form.

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“…However, the nonacidic matrix, THAP has enabled the derivatives to be examined intact with negligible loss of TBDMS groups (Russell et al, 2001). …”

Section: Cyclodextrins and Related Compoundsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Harvey¹

2008

Mass Spectrometry Reviews

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“…99%. The structure of intermediate (3) was confirmed by high-resolution MALDI-TOF-MS [12] using a Voyager Elite XL mass spectrometer equipped with delayed extraction capability (Perceptive Biosystems, Framingham, MA, USA), and 1 H NMR, 13 C NMR, double-quantum filtered 1 H-1 H correlation spectroscopy (COSY) and 1 H- 13 C heteronuclear correlation spectroscopy (HETCOR) using Varian UnityPlus spectrometers (300 MHz and 500 MHz, both from Varian, Walnut Creek, CA, USA). Hexakis(2,3-di-O-methyl-6-dimethyl-t-butylsilyl)-a-CD was then converted into intermediate (4), hexakis(2,3-di-O-methyl)-a-CD, by removing the dimethyl-t-butylsilyl protecting group with hydrogen fluoride (HF) in ethanol.…”

Section: Synthesis Of the Sodium Salt Of Hxdmsmentioning

confidence: 98%

Single‐isomer sulfated α‐cyclodextrins for capillary electrophoresis: Hexakis(2,3‐di‐O‐methyl‐6‐O‐sulfo)‐α‐cyclodextrin, synthesis, analytical characterization, and initial screening tests

Vigh

2004

Electrophoresis

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The third, concluding member of the family of single-isomer, fully sulfated alpha-cyclodextrins, the sodium salt of hexakis(2,3-di-O-methyl-6-O-sulfo)-alpha-cyclodextrin (HxDMS), has been synthesized on the kilogram scale, completing the nine-member array of the single-isomer, 6-O-sulfo CDs now available. HxDMS was tested for the capillary electrophoretic (CE) resolution of the enantiomers of nonelectrolyte, weak acid and weak base analytes contained in our CD screening kit. HxDMS complexed differently with many of the analytes tested than either its larger-ring analogs, heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-CD (HDMS) and octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-CD (ODMS) or its same-ring, but differently substituted analogs, hexakis(6-O-sulfo)-alpha-CD (HxS) and hexakis(2,3-di-O-acetyl-6-O-sulfo)-alpha-CD (HxDAS). For all analytes, the effective mobilities and separation selectivities as a function of the background electrolyte concentration of HxDMS followed the trends that were found for the other single-isomer, 6-O-sulfo CDs.

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“…The eluent flow rate was always kept at 2.0 mL/min and the columns were thermostated at 257C. High-resolution MALDI-TOF-MS measurements of the nonionic CD intermediates and the weak electrolyte CD intermediates were obtained on a Voyager-DE STR Biospectrometry Workstation equipped with delayed extraction capability (Perseptive Biosystems, Framingham, MA, USA) [41]. A 0.1 mM aqueous solution of PEMEDA-BCD was used for the ESI-TOF-MS analysis at the direct aspiration rate of 7 mL/ min and spraying potential of 4500 V on a QSTAR Pulsar instrument (MDS Sciex, Concord, ONT, CN).…”

Section: Synthesis Of Pemeda-bcdmentioning

confidence: 99%

Synthesis of mono‐6‐deoxy‐6‐N,N,N′,N′,N′‐pentamethylethylenediammonio‐cyclomaltoheptaose, a single‐isomer, monosubstituted, permanently dicationic β‐CD and its use for enantiomer separations by CE

Nzeadibe

Vigh

2007

Electrophoresis

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The dichloride salt of mono-6-deoxy-6-N,N,N',N',N'-pentamethylethylenediammonio-cyclomaltoheptaose (PEMEDA-BCD), the first single-isomer, monosubstituted, permanently dicationic beta-CD has been synthesized, analytically characterized, and used for the capillary electrophoretic separation of the enantiomers of a group of analytes in acidic and basic BGEs. When the concentration of PEMEDA-BCD was changed in the BGEs, the resulting effective mobilities of the analytes and the respective separation selectivities followed the predictions of the ionic strength-corrected charged resolving agent migration model. Good separation selectivities and favorable normalized EOF mobilities allowed for the rapid, efficient separation of the enantiomers of anionic, weak acid and nonionic analytes in the low- and/or high-pH BGEs.

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Artifact-free matrix-assisted laser desorption ionization time-of-flight mass spectra of tert.-butyldimethylsilyl ether derivatives of cyclodextrins used for the synthesis of single-isomer, chiral resolving agents for capillary electrophoresis

Cited by 16 publications

References 64 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Single‐isomer sulfated α‐cyclodextrins for capillary electrophoresis: Hexakis(2,3‐di‐O‐methyl‐6‐O‐sulfo)‐α‐cyclodextrin, synthesis, analytical characterization, and initial screening tests

Synthesis of mono‐6‐deoxy‐6‐N,N,N′,N′,N′‐pentamethylethylenediammonio‐cyclomaltoheptaose, a single‐isomer, monosubstituted, permanently dicationic β‐CD and its use for enantiomer separations by CE

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